Sodium Carbonate → HCID 66719161, compound

HRID 882948Notes

Reaction equation

HRID 882948 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][N:3]=1.[Cl:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+]>O.CC(O)C.O.[OH-].[Na+]>[Cl:12][C:13]1[CH:18]=[C:17]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][N:3]=2)[CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 140715712-(6-Chloropyridin-3-yl)acetic acid

Product 1

HCID 66719161HCID 66719161, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 14798Sodium HydroxideSolventHCID 21889133Propan-2-ol--water (1/1)Solvent2×

Conditions

Temperature
67.5 °C

Procedure

2-chloropyridine-5-acetic acid (0.2 gm, 1.21 mmole), 3-chlorophenylboronic acid (0.2 gm, 1.3 mmole) and 50% water wet 10% Palladium carbon (0.08 gm, 0.036 mmole Pd) were added to 10 ml of 5:1 water isopropanol mixture, then Na2CO3 (0.15 gm, 1.4 mmole) dissolved in 3 ml of water was added to the above mixture, the reaction was heated at 65-70° C. overnight, the reaction was cooled to room temperature, diluted with 20 ml of 70:15:1 i-PrOH/H2O/10% NaOH, filtered, the catalyst was washed with 20 ml×3 using the above mixture, the filtrate was dried under vacuum and crude mixture was used without any purification in the next step.

Workup

  1. additionwas added to the above mixture
  2. temperaturethe reaction was cooled to room temperature
  3. filtrationfiltered
  4. washthe catalyst was washed with 20 ml×3 using the above mixture
  5. customthe filtrate was dried under vacuum and crude mixture
  6. customwas used without any purification in the next step

Sources & evidence

ORD record
ord-56d97dacf48a4e04b695c7405a2515d8
Source dataset
uspto-grants-2012_08
Patent number
US08236799B2

Reaction notes

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